4-Hydroxy-2,2,6,6-tetramethylpiperidine → 2,2,6,6-Tetramethyl-1-(prop-2-en-1-yl)piperidin-4-ol

HRID 1199121Notes

Reaction equation

[CH3:1][C:2]1([CH3:11])[CH2:7][CH:6]([OH:8])[CH2:5][C:4]([CH3:10])([CH3:9])[NH:3]1.C(=O)(OCC=C)O[CH2:14][CH:15]=[CH2:16]>Cl[Pd]Cl>[CH2:16]([N:3]1[C:4]([CH3:10])([CH3:9])[CH2:5][CH:6]([OH:8])[CH2:7][C:2]1([CH3:11])[CH3:1])[CH:15]=[CH2:14]

Participants

Conditions

Temperature: 110 °C

Procedure

2,2,6,6-tetramethyl-piperidin-4ol (0.5 g, 3.18 mmol), PdCl2 (20 mg, 0.11 mmol) and di-allyl carbonate (5 ml, 36 mmol) are charged, under inert atmosphere, into a 10 ml-flask equipped with a reflux condenser. The reaction mixture is then heated to 110° C. under stirring for about 6 hours. Gas-chromatographic analysis shows that the reaction afforded the desired 1-allyl-2,2,6,6-tetramethyl-piperidin-4ol in 85% yield (calculated on the starting piperidinol) and >98% selectivity.

Workup

customequipped with a reflux condenser

Sources & evidence

ORD record: ord-582aeb7cedf34bfe828de06d85c5a0b5
Source dataset: uspto-grants-1990_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04898946

Reaction notes

Loading…